3-苄基若丹宁

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-benzylrhodanine (0.50 g, 2.2 mmol), benzaldehyde (0.23 mL, 2.3 mmol) and TEA (0.68 mL, 4.9 mmol) in MeCN (5 mL, anhyd) was heated at reflux. After 2 h the reaction mixture was cooled. Precipitated solids were collected by filtration, triturated with MeCN-Hex and dried under vacuum to yield 3-benzyl-5-benzylidene-2-thioxothiazolidin-4-one, which was used without further purification. anhyd) was heated at reflux After 2 h the reaction mixture was cooled Precipitated solids were collected by filtration triturated with MeCN-Hex dried under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-benzylrhodanine (0.50 g, 2.2 mmol), benzaldehyde (0.23 mL, 2.3 mmol) and TEA (0.68 mL, 4.9 mmol) in MeCN (5 mL, anhyd) was heated at reflux. After 2 h the reaction mixture was cooled. Precipitated solids were collected by filtration, triturated with MeCN-Hex and dried under vacuum to yield 3-benzyl-5-benzylidene-2-thioxothiazolidin-4-one, which was used without further purification. anhyd) was heated at reflux After 2 h the reaction mixture was cooled Precipitated solids were collected by filtration triturated with MeCN-Hex dried under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of TMOF-toluene (1:1, 6 mL, anhyd) was added N-methylaniline (0.33 mL, 3.0 mmol) and 3-benzylrhodanine (0.67 g, 3.0 mmol). After heating at reflux for 2 h, the reaction mixture was cooled, concentrated and chromatographed (silica gel, 0:100 to 40:60 EtOAc-Hex) to yield the title product (0.40 g, 39%) as a yellow solid. 1H-NMR (CDCl3): δ 7.79 (1H, s), 7.34-7.47 (5H, m), 7.17-7.31 (5H, m), 5.25 (2H, s), 3.54 (3H, s). After heating at reflux for 2 h the reaction mixture was cooled concentrated chromatographed (silica gel, 0:100 to 40:60 EtOAc-Hex)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 30 ml of an ethanol solution of 13.0 g of the intermediate product obtained in Preparative Example 2, viz., 2-ethylmercapto-3-ethylbenzothiazolium p-toluenesulfoante, was added 4.5 g of 3-benzylrhodanine, while stirring the mixture at room temperature (about 20° C.), 6.1 g of triethylamine was added dropwise to the mixture over a 3 minute period, and thereafter, the resultant mixture was refluxed for 10 minutes. After cooling the reaction mixture, precipitate formed was recovered by filtration and recrystallized from a mixture of chloroform and ethanol to provide 4.6 g of 3-benzyl-5-(3-ethylbenzothiazolylidene)rhodanine (melting point 209° to 211° C.). was added dropwise to the mixture over a 3 minute period After cooling the reaction mixture, precipitate formed was recovered by filtration recrystallized from a mixture of chloroform and ethanol

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 30 ml of an ethanol solution of 13.0 g of the intermediate product obtained in Preparative Example 2, viz., 2-ethylmercapto-3-ethylbenzothiazolium p-toluenesulfoante, was added 4.5 g of 3-benzylrhodanine, while stirring the mixture at room temperature (about 20° C.), 6.1 g of triethylamine was added dropwise to the mixture over a 3 minute period, and thereafter, the resultant mixture was refluxed for 10 minutes. After cooling the reaction mixture, precipitate formed was recovered by filtration and recrystallized from a mixture of chloroform and ethanol to provide 4.6 g of 3-benzyl-5-(3-ethylbenzothiazolylidene)rhodanine (melting point 209° to 211° C.). was added dropwise to the mixture over a 3 minute period After cooling the reaction mixture, precipitate formed was recovered by filtration recrystallized from a mixture of chloroform and ethanol

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-benzylrhodanine (0.50 g, 2.2 mmol), benzaldehyde (0.23 mL, 2.3 mmol) and TEA (0.68 mL, 4.9 mmol) in MeCN (5 mL, anhyd) was heated at reflux. After 2 h the reaction mixture was cooled. Precipitated solids were collected by filtration, triturated with MeCN-Hex and dried under vacuum to yield 3-benzyl-5-benzylidene-2-thioxothiazolidin-4-one, which was used without further purification. anhyd) was heated at reflux After 2 h the reaction mixture was cooled Precipitated solids were collected by filtration triturated with MeCN-Hex dried under vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of TMOF-toluene (1:1, 6 mL, anhyd) was added N-methylaniline (0.33 mL, 3.0 mmol) and 3-benzylrhodanine (0.67 g, 3.0 mmol). After heating at reflux for 2 h, the reaction mixture was cooled, concentrated and chromatographed (silica gel, 0:100 to 40:60 EtOAc-Hex) to yield the title product (0.40 g, 39%) as a yellow solid. 1H-NMR (CDCl3): δ 7.79 (1H, s), 7.34-7.47 (5H, m), 7.17-7.31 (5H, m), 5.25 (2H, s), 3.54 (3H, s). After heating at reflux for 2 h the reaction mixture was cooled concentrated chromatographed (silica gel, 0:100 to 40:60 EtOAc-Hex)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To 30 ml of an ethanol solution of 13.0 g of the intermediate product obtained in Preparative Example 2, viz., 2-ethylmercapto-3-ethylbenzothiazolium p-toluenesulfoante, was added 4.5 g of 3-benzylrhodanine, while stirring the mixture at room temperature (about 20° C.), 6.1 g of triethylamine was added dropwise to the mixture over a 3 minute period, and thereafter, the resultant mixture was refluxed for 10 minutes. After cooling the reaction mixture, precipitate formed was recovered by filtration and recrystallized from a mixture of chloroform and ethanol to provide 4.6 g of 3-benzyl-5-(3-ethylbenzothiazolylidene)rhodanine (melting point 209° to 211° C.). was added dropwise to the mixture over a 3 minute period After cooling the reaction mixture, precipitate formed was recovered by filtration recrystallized from a mixture of chloroform and ethanol